Natural Product: NPC476662

Natural Product ID:  NPC476662
Common Name:   Kipukasin B
IUPAC Name:   [(2R,3R,4S,5S)-4-acetyloxy-5-[(2,4-dioxopyrimidin-1-yl)methyl]-2-(hydroxymethyl)oxolan-3-yl] 4-hydroxy-2-methoxy-6-methylbenzoate
Synonyms:  
Molecular Formula:   C21H24N2O10
Standard InCHIKey:  NMEFMJWRPAEIMY-QGWWYQLQSA-N
Standard InCHI:  InChI=1S/C21H24N2O10/c1-10-6-12(26)7-13(30-3)17(10)20(28)33-19-15(9-24)32-14(18(19)31-11(2)25)8-23-5-4-16(27)22-21(23)29/h4-7,14-15,18-19,24,26H,8-9H2,1-3H3,(H,22,27,29)/t14-,15+,18-,19+/m0/s1
Canonical SMILES:  OC[C@H]1O[C@H]([C@@H]([C@@H]1OC(=O)c1c(C)cc(cc1OC)O)OC(=O)C)Cn1ccc(nc1=O)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO15067 Aspergillus versicolor Species Aspergillaceae Eukaryota isolated from the surface of a basidioma of Gandoderma australe found growing on a living tree in a montane mesic forest Kipuka Pauula (Bird Park), Volcanoes National Park, Hawaii PMID[17608440]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 12 mm 17608440

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC476662 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9944 High Similarity NPC476661
0.7947 Intermediate Similarity NPC477816
0.794 Intermediate Similarity NPC286135
0.7889 Intermediate Similarity NPC200773
0.7889 Intermediate Similarity NPC240768
0.7842 Intermediate Similarity NPC309692
0.7828 Intermediate Similarity NPC83019
0.779 Intermediate Similarity NPC215921
0.779 Intermediate Similarity NPC70016
0.7778 Intermediate Similarity NPC204580
0.7732 Intermediate Similarity NPC18306
0.7725 Intermediate Similarity NPC129578
0.7697 Intermediate Similarity NPC280404
0.7697 Intermediate Similarity NPC86373
0.7697 Intermediate Similarity NPC210425
0.7697 Intermediate Similarity NPC277426
0.7653 Intermediate Similarity NPC469437
0.7637 Intermediate Similarity NPC469670
0.7637 Intermediate Similarity NPC469619
0.7621 Intermediate Similarity NPC293347
0.7612 Intermediate Similarity NPC313453
0.7584 Intermediate Similarity NPC474385
0.7581 Intermediate Similarity NPC77679
0.7581 Intermediate Similarity NPC84935
0.7581 Intermediate Similarity NPC190020
0.7577 Intermediate Similarity NPC473562
0.7569 Intermediate Similarity NPC210320
0.7565 Intermediate Similarity NPC329816
0.7561 Intermediate Similarity NPC475768
0.7561 Intermediate Similarity NPC80472
0.7561 Intermediate Similarity NPC314946
0.7542 Intermediate Similarity NPC51106
0.7541 Intermediate Similarity NPC179178
0.7528 Intermediate Similarity NPC158634
0.7527 Intermediate Similarity NPC215711
0.7527 Intermediate Similarity NPC150227
0.7527 Intermediate Similarity NPC73411
0.7524 Intermediate Similarity NPC79130
0.7487 Intermediate Similarity NPC246466
0.7486 Intermediate Similarity NPC270160
0.7486 Intermediate Similarity NPC476684
0.7486 Intermediate Similarity NPC237440
0.7476 Intermediate Similarity NPC246303
0.7473 Intermediate Similarity NPC472036
0.7473 Intermediate Similarity NPC99381
0.7473 Intermediate Similarity NPC16082
0.7473 Intermediate Similarity NPC82592
0.7473 Intermediate Similarity NPC478230
0.7473 Intermediate Similarity NPC69043
0.7473 Intermediate Similarity NPC79998
0.7473 Intermediate Similarity NPC199926
0.7472 Intermediate Similarity NPC158472
0.7459 Intermediate Similarity NPC478224
0.745 Intermediate Similarity NPC94499
0.7447 Intermediate Similarity NPC279732
0.7446 Intermediate Similarity NPC96501
0.7444 Intermediate Similarity NPC469542
0.7432 Intermediate Similarity NPC471641
0.7432 Intermediate Similarity NPC471642
0.7432 Intermediate Similarity NPC240253
0.7432 Intermediate Similarity NPC240622
0.743 Intermediate Similarity NPC475730
0.743 Intermediate Similarity NPC90411
0.743 Intermediate Similarity NPC67650
0.743 Intermediate Similarity NPC1704
0.7419 Intermediate Similarity NPC137301
0.7419 Intermediate Similarity NPC281477
0.7416 Intermediate Similarity NPC32360
0.7416 Intermediate Similarity NPC247409
0.7407 Intermediate Similarity NPC472055
0.7394 Intermediate Similarity NPC472889
0.7389 Intermediate Similarity NPC469579
0.7385 Intermediate Similarity NPC5674
0.738 Intermediate Similarity NPC472890
0.738 Intermediate Similarity NPC170189
0.738 Intermediate Similarity NPC208173
0.7368 Intermediate Similarity NPC117985
0.7366 Intermediate Similarity NPC184284
0.7366 Intermediate Similarity NPC115249
0.7366 Intermediate Similarity NPC76041
0.7366 Intermediate Similarity NPC316164
0.7366 Intermediate Similarity NPC167903
0.7363 Intermediate Similarity NPC83272
0.7363 Intermediate Similarity NPC472034
0.7358 Intermediate Similarity NPC283041
0.7354 Intermediate Similarity NPC470339
0.7352 Intermediate Similarity NPC470847
0.7351 Intermediate Similarity NPC472891
0.7348 Intermediate Similarity NPC472006
0.7344 Intermediate Similarity NPC191930
0.734 Intermediate Similarity NPC227062
0.733 Intermediate Similarity NPC2173
0.733 Intermediate Similarity NPC202771
0.733 Intermediate Similarity NPC328700
0.733 Intermediate Similarity NPC119818
0.7327 Intermediate Similarity NPC475442
0.7327 Intermediate Similarity NPC252156
0.7326 Intermediate Similarity NPC478231
0.7323 Intermediate Similarity NPC475566
0.7322 Intermediate Similarity NPC107625
0.7322 Intermediate Similarity NPC472033
0.732 Intermediate Similarity NPC329992
0.7318 Intermediate Similarity NPC268052
0.7316 Intermediate Similarity NPC470358
0.7308 Intermediate Similarity NPC184702
0.7308 Intermediate Similarity NPC470932
0.7306 Intermediate Similarity NPC20237
0.7306 Intermediate Similarity NPC314987
0.7303 Intermediate Similarity NPC135837
0.7302 Intermediate Similarity NPC478225
0.7302 Intermediate Similarity NPC473395
0.7294 Intermediate Similarity NPC475624
0.7293 Intermediate Similarity NPC250755
0.7293 Intermediate Similarity NPC82913
0.7292 Intermediate Similarity NPC249181
0.7287 Intermediate Similarity NPC317585
0.7287 Intermediate Similarity NPC478221
0.7283 Intermediate Similarity NPC53362
0.7283 Intermediate Similarity NPC8817
0.7283 Intermediate Similarity NPC166583
0.7282 Intermediate Similarity NPC221792
0.7277 Intermediate Similarity NPC35345
0.7273 Intermediate Similarity NPC206061
0.7273 Intermediate Similarity NPC271681
0.7268 Intermediate Similarity NPC312789
0.7268 Intermediate Similarity NPC254053
0.7263 Intermediate Similarity NPC33144
0.7263 Intermediate Similarity NPC94248
0.7263 Intermediate Similarity NPC478200
0.7263 Intermediate Similarity NPC212693
0.7259 Intermediate Similarity NPC99723
0.7258 Intermediate Similarity NPC56204
0.7254 Intermediate Similarity NPC7752
0.7253 Intermediate Similarity NPC478202
0.7251 Intermediate Similarity NPC14390
0.7249 Intermediate Similarity NPC472050
0.7249 Intermediate Similarity NPC54928
0.7248 Intermediate Similarity NPC475292
0.7248 Intermediate Similarity NPC475565
0.7248 Intermediate Similarity NPC475349
0.7243 Intermediate Similarity NPC470359
0.7243 Intermediate Similarity NPC153417
0.7241 Intermediate Similarity NPC264938
0.7231 Intermediate Similarity NPC117713
0.7231 Intermediate Similarity NPC292213
0.7228 Intermediate Similarity NPC85734
0.7228 Intermediate Similarity NPC32058
0.7228 Intermediate Similarity NPC473023
0.7228 Intermediate Similarity NPC260946
0.7228 Intermediate Similarity NPC470357
0.7225 Intermediate Similarity NPC200594
0.7222 Intermediate Similarity NPC312630
0.7222 Intermediate Similarity NPC324220
0.722 Intermediate Similarity NPC185031
0.7213 Intermediate Similarity NPC66404
0.7213 Intermediate Similarity NPC95123
0.7213 Intermediate Similarity NPC27106
0.7211 Intermediate Similarity NPC478226
0.7211 Intermediate Similarity NPC26353
0.7207 Intermediate Similarity NPC70380
0.7206 Intermediate Similarity NPC308709
0.7198 Intermediate Similarity NPC297985
0.7196 Intermediate Similarity NPC16286
0.7196 Intermediate Similarity NPC473241
0.7196 Intermediate Similarity NPC279218
0.7196 Intermediate Similarity NPC108937
0.7191 Intermediate Similarity NPC182496
0.7191 Intermediate Similarity NPC180905
0.719 Intermediate Similarity NPC314596
0.7189 Intermediate Similarity NPC137296
0.7189 Intermediate Similarity NPC202494
0.7188 Intermediate Similarity NPC69868
0.7188 Intermediate Similarity NPC92589
0.7188 Intermediate Similarity NPC96031
0.7188 Intermediate Similarity NPC317544
0.7181 Intermediate Similarity NPC256141
0.7181 Intermediate Similarity NPC273483
0.7181 Intermediate Similarity NPC475116
0.7181 Intermediate Similarity NPC295646
0.7179 Intermediate Similarity NPC473094
0.7179 Intermediate Similarity NPC249977
0.7174 Intermediate Similarity NPC297788
0.7174 Intermediate Similarity NPC134621
0.7174 Intermediate Similarity NPC257558
0.7174 Intermediate Similarity NPC75694
0.717 Intermediate Similarity NPC197125
0.7167 Intermediate Similarity NPC126739
0.7167 Intermediate Similarity NPC197666
0.7167 Intermediate Similarity NPC191835
0.7167 Intermediate Similarity NPC472602
0.7166 Intermediate Similarity NPC470908
0.7166 Intermediate Similarity NPC119929
0.7166 Intermediate Similarity NPC327059
0.7166 Intermediate Similarity NPC321387
0.7166 Intermediate Similarity NPC295036
0.7166 Intermediate Similarity NPC475460
0.7164 Intermediate Similarity NPC162694
0.7163 Intermediate Similarity NPC478048
0.7158 Intermediate Similarity NPC78554
0.7158 Intermediate Similarity NPC475797

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC476662 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7766 Intermediate Similarity NPD3473 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD5710 Approved
0.7701 Intermediate Similarity NPD5711 Approved
0.7617 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7565 Approved
0.7415 Intermediate Similarity NPD6863 Phase 2
0.733 Intermediate Similarity NPD5006 Approved
0.733 Intermediate Similarity NPD5005 Approved
0.7318 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD8469 Approved
0.7277 Intermediate Similarity NPD7930 Approved
0.7273 Intermediate Similarity NPD6973 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4363 Phase 3
0.7241 Intermediate Similarity NPD4360 Phase 2
0.7206 Intermediate Similarity NPD4361 Phase 2
0.7206 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD5353 Approved
0.7174 Intermediate Similarity NPD2533 Approved
0.7174 Intermediate Similarity NPD2534 Approved
0.7174 Intermediate Similarity NPD2532 Approved
0.7156 Intermediate Similarity NPD7585 Approved
0.7136 Intermediate Similarity NPD4420 Approved
0.7123 Intermediate Similarity NPD8151 Discontinued
0.7113 Intermediate Similarity NPD5242 Approved
0.7109 Intermediate Similarity NPD7584 Approved
0.7109 Intermediate Similarity NPD7583 Approved
0.7101 Intermediate Similarity NPD7810 Phase 3
0.7101 Intermediate Similarity NPD7811 Phase 3
0.7088 Intermediate Similarity NPD2654 Approved
0.7075 Intermediate Similarity NPD7701 Phase 2
0.7074 Intermediate Similarity NPD4380 Phase 2
0.7072 Intermediate Similarity NPD8059 Phase 3
0.7072 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD3817 Phase 2
0.7014 Intermediate Similarity NPD8319 Approved
0.7014 Intermediate Similarity NPD8320 Phase 1
0.701 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7874 Approved
0.7009 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD3818 Discontinued
0.7 Intermediate Similarity NPD8366 Approved
0.6991 Remote Similarity NPD4377 Discontinued
0.6977 Remote Similarity NPD7783 Phase 2
0.6977 Remote Similarity NPD7801 Approved
0.6977 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6232 Discontinued
0.6963 Remote Similarity NPD7819 Suspended
0.6961 Remote Similarity NPD6836 Approved
0.6951 Remote Similarity NPD8491 Approved
0.6946 Remote Similarity NPD5037 Approved
0.6946 Remote Similarity NPD5038 Approved
0.6943 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6943 Remote Similarity NPD7075 Discontinued
0.6942 Remote Similarity NPD4466 Phase 1
0.6938 Remote Similarity NPD8285 Discontinued
0.6931 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7177 Discontinued
0.6919 Remote Similarity NPD6823 Phase 2
0.6911 Remote Similarity NPD6801 Discontinued
0.6911 Remote Similarity NPD1934 Approved
0.6903 Remote Similarity NPD8067 Phase 3
0.6901 Remote Similarity NPD7999 Approved
0.6897 Remote Similarity NPD5036 Approved
0.6891 Remote Similarity NPD3882 Suspended
0.6884 Remote Similarity NPD7054 Approved
0.6875 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2801 Approved
0.6869 Remote Similarity NPD7473 Discontinued
0.6862 Remote Similarity NPD8461 Discontinued
0.6859 Remote Similarity NPD6385 Approved
0.6859 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6859 Remote Similarity NPD6386 Approved
0.685 Remote Similarity NPD7472 Approved
0.6845 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6799 Approved
0.6842 Remote Similarity NPD7282 Approved
0.684 Remote Similarity NPD8162 Phase 2
0.684 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6839 Remote Similarity NPD5402 Approved
0.6839 Remote Similarity NPD7318 Phase 3
0.6832 Remote Similarity NPD5028 Approved
0.6832 Remote Similarity NPD5026 Approved
0.6832 Remote Similarity NPD36 Approved
0.6832 Remote Similarity NPD4954 Approved
0.6832 Remote Similarity NPD4955 Approved
0.6832 Remote Similarity NPD5034 Approved
0.6832 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6782 Approved
0.6825 Remote Similarity NPD6780 Approved
0.6825 Remote Similarity NPD6777 Approved
0.6825 Remote Similarity NPD6781 Approved
0.6825 Remote Similarity NPD6779 Approved
0.6825 Remote Similarity NPD6776 Approved
0.6825 Remote Similarity NPD6778 Approved
0.6818 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6166 Phase 2
0.6816 Remote Similarity NPD6797 Phase 2
0.6804 Remote Similarity NPD4868 Clinical (unspecified phase)
0.68 Remote Similarity NPD6020 Phase 2
0.6796 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6746 Phase 2
0.6782 Remote Similarity NPD7251 Discontinued
0.6782 Remote Similarity NPD6559 Discontinued
0.6782 Remote Similarity NPD5030 Phase 2
0.6782 Remote Similarity NPD7039 Approved
0.6782 Remote Similarity NPD7038 Approved
0.6777 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7907 Approved
0.6771 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6769 Remote Similarity NPD5219 Approved
0.6769 Remote Similarity NPD5218 Approved
0.6766 Remote Similarity NPD7074 Phase 3
0.6757 Remote Similarity NPD4111 Phase 1
0.6757 Remote Similarity NPD4665 Approved
0.6757 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1511 Approved
0.6749 Remote Similarity NPD7808 Phase 3
0.6737 Remote Similarity NPD5403 Approved
0.6736 Remote Similarity NPD7317 Phase 3
0.6736 Remote Similarity NPD6844 Discontinued
0.6734 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6734 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6734 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6729 Remote Similarity NPD7435 Discontinued
0.6729 Remote Similarity NPD7698 Approved
0.6729 Remote Similarity NPD7696 Phase 3
0.6729 Remote Similarity NPD7697 Approved
0.672 Remote Similarity NPD4378 Clinical (unspecified phase)
0.672 Remote Similarity NPD3157 Approved
0.672 Remote Similarity NPD3158 Phase 1
0.672 Remote Similarity NPD3688 Clinical (unspecified phase)
0.672 Remote Similarity NPD3146 Approved
0.6719 Remote Similarity NPD6599 Discontinued
0.6719 Remote Similarity NPD4678 Approved
0.6719 Remote Similarity NPD4675 Approved
0.6717 Remote Similarity NPD7315 Approved
0.6716 Remote Similarity NPD5844 Phase 1
0.6716 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6714 Remote Similarity NPD2494 Approved
0.6714 Remote Similarity NPD2493 Approved
0.6714 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6712 Remote Similarity NPD7827 Phase 1
0.67 Remote Similarity NPD5029 Approved
0.67 Remote Similarity NPD5027 Approved
0.67 Remote Similarity NPD5031 Approved
0.6699 Remote Similarity NPD8150 Discontinued
0.6698 Remote Similarity NPD7871 Phase 2
0.6698 Remote Similarity NPD7870 Phase 2
0.6697 Remote Similarity NPD7047 Phase 3
0.6685 Remote Similarity NPD1510 Phase 2
0.6684 Remote Similarity NPD1512 Approved
0.6684 Remote Similarity NPD1309 Phase 2
0.6684 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6684 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6684 Remote Similarity NPD1307 Phase 2
0.6683 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6681 Remote Similarity NPD7048 Phase 3
0.6667 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6959 Discontinued
0.6667 Remote Similarity NPD6997 Phase 2
0.6667 Remote Similarity NPD2649 Approved
0.6667 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD824 Approved
0.6667 Remote Similarity NPD1898 Discontinued
0.6667 Remote Similarity NPD2651 Approved
0.6651 Remote Similarity NPD7497 Discontinued
0.6651 Remote Similarity NPD7296 Approved
0.665 Remote Similarity NPD1252 Clinical (unspecified phase)
0.6649 Remote Similarity NPD3692 Discontinued
0.6649 Remote Similarity NPD6032 Approved
0.6649 Remote Similarity NPD1670 Discontinued
0.6648 Remote Similarity NPD2238 Phase 2
0.6637 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6636 Remote Similarity NPD7263 Phase 2
0.6636 Remote Similarity NPD3450 Approved
0.6636 Remote Similarity NPD3452 Approved
0.6634 Remote Similarity NPD5035 Approved
0.6633 Remote Similarity NPD6808 Phase 2
0.6633 Remote Similarity NPD7608 Discontinued
0.6632 Remote Similarity NPD5401 Approved
0.662 Remote Similarity NPD4582 Approved
0.662 Remote Similarity NPD4583 Approved
0.662 Remote Similarity NPD6874 Approved
0.6615 Remote Similarity NPD3686 Approved
0.6615 Remote Similarity NPD5773 Approved
0.6615 Remote Similarity NPD3687 Approved
0.6615 Remote Similarity NPD4210 Discontinued
0.6615 Remote Similarity NPD5772 Approved
0.6613 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6613 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6604 Remote Similarity NPD2974 Approved
0.6604 Remote Similarity NPD2975 Approved
0.6604 Remote Similarity NPD2973 Approved
0.6599 Remote Similarity NPD3749 Approved
0.6598 Remote Similarity NPD7411 Suspended
0.6598 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5890 Approved

Structure

External Identifiers

PubChem CID   44445675
ChEMBL   CHEMBL398650
ZINC  

Physicochemical Properties

Molecular Weight:  464.14
ALogP:  -1.8393
MLogP:  2.45
XLogP:  0.286
# Rotatable Bonds:  15
Polar Surface Area:  164.42
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  33

Download Data

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Structure MOL file  
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Biological Activities  
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